Although he guided the team to seven World Series titles during his 37 years as owner of the New York Yankees, Steinbrenner’s management of his team wasn’t always exemplary. After their loss to the Dodgers in the 1981 World Series, the Bronx Bombers made only one post season appearance in fourteen years. A three year ban from day-to-day operations beginning in 1990 allowed GM Gene Michaels and Buck Showalter to rebuild the without his interference. The built by Michaels and Showalter would go on to win four championships in the late ’90s but thanks to ‘the Boss’ they weren’t around to enjoy the fruits of their labor…

File photo of the late George Steinbrenner. (Photo by: Stephen Dunn/Getty Images)

4 – James Dolan, The New York KNicks and New York Rangers

James Dolan has the dubious honor of being a failure as an owner in two major North American sports leagues. As the principle manager of the Knicks and the Rangers since 1994, Dolan’s the first name New Yorkers mention when asked why those two teams have been mired in mediocrity for decades. High profile free agents that have flopped, the disastrous hiring of Isiah Thomas as Knicks team president, the failure of the Rangers to win a Stanley Cup despite a roster stocked with talent all can be laid on Dolan’s shoulders. You could say his only “success” has been keeping fans coming to games at Madison Square Garden at all!.

File photo of James Dolan. (Photo by Fernando Leon/Getty Images)

3 – Marge Schott, The Cincinnati Reds

Marge Schott is a name that’s become infamous in major league baseball, and her relationship with the game and Reds fans is a complicated one. On the one hand, she holds the distinction of being only the third woman in North American major league sports history to own a franchise that she did not inherit. She was beloved by fans of the Reds for years for keeping ticket and concession prices low and for sitting in the stands with fans for every game, and taking photos with them whenever they asked. She never had kids of her own, but famously allowed kids on the field before games to run out to deep center field and back. That said, all the good will she had earned with fans could not make up for the nickle-and-dime approach she took to the running the team which kept them from from being contenders. Then there’s the racist remarks Schott made about African Americans, Jews and people of Japanese descent. She was banned from day-to-day operations of the Reds twice, in 1993 and then again in 1996, for her inflammatory comments. After being reinstated in 1998, Schott faced yet another suspension in 1999 and chose to resign instead of being ousted by her own business partners.

A shrewd businessman, Snyder’s Washington Redskins are worth well over $1.5 Billion according to Forbes. However, the Redskins faithful would be much happier if the billionaire’s football knowledge matched his business acumen. Snyder, a man who has sued season ticket holders and banned signs from his stadium, has done little to gain respect from DC fans. His high-profile expensive free agent signings that have flopped – Bruce Smith, Donovan McNabb, and others – shows an more of an interest in marketing value than actual production on the field. However, his biggest problem might just be the revolving door of head coaches, as the Redskins are no moving on to their eighth coach of Snyder’s 15-season tenure. Snyder has also become a lightning rod over the name of his team as many view the term ‘Redskins’ as racially insensitive.

The one-time Montreal Expos and current Miami Marlins owner may in fact be one of the most hated men in professional sports. In 2002, he helped orchestrate the sale of the Expos to the MLB commisioner’s office, while at the same time acquiring the Marlins from John Henry for $158 million. That series of moves earned him theire of a huge number of Canadian baseball fans and landed him in federal court as the principle defendant in a racketeering lawsuit brought against him and major league baseball by his former Expo business partners. But all that pales incomparison with hsi recent handling of the Marlins, who boasted a new everything in 2012 — a new publicly-funded stadium, a new coach, new star players, even a new name. It should have been a fresh chapter for a franchise desperately trying to turn the page from the penny-pinching, high-turnover team of old. But the team finished last that seasn, and in the aftermath, Loria shed just under $70 million in payroll by trading away the stars acquired barely a year before. The result? In 2013 they finished last in the NL East again with a 62 – 100 record!